Substituted aminophenyluracils

ABSTRACT

The invention relates to novel substituted aminophenyluracils of the general formula (I)                    
     to a process for their preparation and to their use as herbicides and insecticides.

This is a continuation-in-part of U.S. application Ser. No. 08/945,768,filed Oct. 31, 1997 (now pending), which was filed under 35 USC 371 andwhich was accorded International Application No. PCT/EP96/01722 and anInternational Filing Date of Apr. 25,1996.

The invention relates to novel substituted aminophenyluracils, to aprocess for their preparation and to their use as herbicides andinsecticides.

It is known that certain substituted aminophenyluracils have herbicidalproperties (cf. EP-408 382/U.S. Pat. No. 5 084 084/U.S. Pat. No. 5 127935/U.S. Pat. No. 5 154 755, EP-563 384, DE-44 12 079), but they havehitherto not attained any major importance either as herbicides or asinsecticides.

This invention, accordingly, provides the novel substitutedaminophenyluracils of the general formula (I)

in which

Q represents oxygen or sulphur,

R¹ represents hydrogen, cyano or halogen,

R² represents cyano, thiocarbamoyl, halogen or represents optionallysubstituted alkyl,

R³ represents respectively optionally substituted alkyl, cycloalkyl,aryl, arylalkyl or heteroaryl,

R⁴ represents respectively optionally substituted cycloalkyl, aryl orheteroaryl,

R⁵ represents hydrogen, halogen or represents respectively optionallysubstituted alkyl or alkoxy,

R⁶ represents optionally substituted alkyl and

R⁷ represents hydrogen, hydroxyl, amino or represents respectivelyoptionally substituted alkyl, alkoxy, alkenyl or alkinyl.

The novel substituted aminophenyluracils of the general formula (I) areobtained when appropriate sulphonylaminophenyluracils of the generalformula (II)

in which

Q, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are each as defined above, are reactedwith acid derivatives of the general formula (III)

R⁴—CO—X  (III)

in which

R⁴ is as definied above and

X represents halogen or the grouping —CO—R⁴,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent.

The novel substituted aminophenyluracils of the general formula (I) havestrong herbicidal and insecticidal activity.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkenyl or alkinyl, are in each case straight-chain orbranched.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

The invention preferably provides compounds of the formula (I) in which

Q represents oxygen or sulphur,

R¹ represents hydrogen, cyano, fluorine or chlorine,

R² represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, orrepresents optionally fluorine- and/or chlorine-substituted alkyl having1 to 4 carbon atoms,

R³ represents optionally cyano-, fluorine-, chlorine-, bromine-,C₁-C₄-alkoxy- or C₁-C₄-alkylthio-substituted alkyl having 1 to 6 carbonatoms,

R³ furthermore represents optionally cyano-, fluorine-, chlorine-,bromine- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 8 carbonatoms,

R³ furthermore represents phenyl, naphthyl, benzyl, phenylethyl,thienyl, pyrazolyl, pyridinyl or quinolinyl, possible substituents ineach case being:

fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl,thiocarbamoyl, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,dimethylaminosulphonyl, diethylaminosulphonyl, respectively optionallyfluorine- and/or chlorine-substituted C₁-C₄-alkylsulphinyl orC₁-C₄-alkylsulphonyl, respectively optionally, fluorine-, chlorine-,bromine-, cyano-, methoxy- or ethoxy-substituted C₁-C₄-alkoxycarbonyl orrespectively optionally fluorine-, chlorine-, bromine-, cyano-, methyl-,methoxy-, trifluoromethyl- and/or trifluoromethoxy-substituted phenyl,phenyloxy or phenylthio;

R⁴ represents optionally cyano-, fluorine-, chlorine-, bromine- orC₁-C₄-alkyl-substituted cycloalkyl having 3 to 8 carbon atoms,

R⁴ furthermore represents respectively optionally substituted phenyl,naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl,pyrimidinyl or quinolinyl, possible substituents in each case being:fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl,thiocarbamoyl, dimethylamino, dimethylaminosulphonyl,diethylaminosulphonyl, respectively optionally fluorine- and/orchlorine-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphinyl or C₁-C₄-alkylsulphonyl or optionally fluorine-,chlorine-, bromine-, cyano-, methoxy- or ethoxy-substitutedC₁-C₄-alkoxycarbonyl;

R⁵ represents hydrogen, fluorine, chlorine, bromine or representsrespectively optionally fluorine- and/or chlorine-substituted alkyl oralkoxy having in each case 1 to 4 carbon atoms,

R⁶ represents optionally fluorine- and/or chlorine-substituted alkylhaving 1 to 4 carbon atoms and

R⁷ represents hydrogen, hydroxyl, amino or represents respectivelyoptionally fluorine-, chlorine- or C₁-C₄-alkoxy-substituted alkyl,alkoxy, alkenyl or alkinyl having in each case up to 6 carbon atoms.

The invention in particular provides compounds of the formula (I) inwhich

Q represents oxygen or sulphur,

R¹ represents hydrogen, cyano, fluorine or chlorine,

R² represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, methyl,ethyl, n-or i-propyl, n-, i-, s- or t-butyl or trifluoromethyl,

R³ represents respectively optionally cyano-, fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl,

R³ furthermore represents respectively optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

R³ furthermore represents respectively optionally substituted phenyl,naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl, pyridinyl orquinolinyl, possible substituents being: fluorine, chlorine, bromine,cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- ori-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl,dimethylaminosulphonyl, diethylaminosulphonyl, methoxycarbonyl,ethoxycarbonyl, n-or i-propoxycarbonyl,

R⁴ represents optionally cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n-or i-propyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl,

R⁴ furthermore represents respectively optionally substituted phenyl,naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, pyridinyl orpyrimidinyl, possible substituents in each case being: fluorine,chlorine, bromine, cyano, nitro, carboxy, carbamoyl, thiocarbamoyl,dimethylamino, dimethylaminosulphonyl or diethylaminosulphonyl,respectively optionally fluorine- and/or chlorine-substituted methyl,ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- ori-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- ori-propylsulphonyl, respectively optionally fluorine-, chlorine-,bromine-, cyano-, methoxy- or ethoxy-substituted methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, respectively optionallyfluorine-, chlorine-, bromine-, cyano-, methyl-, methoxy-,trifluormethyl- and/or trifluoromethoxy-substituted phenyl, phenyloxy orphenylthio,

R⁵ represents hydrogen, fluorine, chlorine, bromine or representsrespectively optionally fluorine- and/or chlorine-substituted methyl,ethyl, n- or i-propyl,

R⁶ represents optionally fluorine- and/or chlorine-substituted methyl,ethyl, n- or i-propyl and

R⁷ represents hydrogen, amino or represents respectively optionallyfluorine-and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-,i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy,propenyl, butenyl, propinyl or butinyl.

The general of preferred radical definitions listed above are validradicals for the end products of formula (I) and also, in acorresponding manner, for the starting materials or intermediates whichare required in each case for the preparation. These radical definitionscan be combined with each other at will, i.e. combinations between thegiven preferred ranges are also possible.

Using, for example,1-(4-chloro-2-fluoro-5-methylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-3,4-dimethyl-1(2H)-pyrimidineand 2-fluoro-benzoyl chloride as starting materials, the course of thereaction in the process according to the invention can be illustrated bythe following scheme:

The formula (II) provides a general definition of thesulphonylaminophenyl-uracils to be used as starting materials in theprocess according to the invention for preparing the compounds of theformula (I). In the formula (II), Q, R¹, R², R³, R⁵, R⁶ and R⁷ eachpreferably or in particular have those meanings which have already beenindicated above, in connection with the description of the compounds ofthe formula (I) to be prepared according to the invention, as beingpreferred or particularly preferred for Q, R¹, R², R³, R⁵, R⁶ and R⁷.

The starting materials of the formula (II) are known and/or can beprepared by process known per se (cf. EP-408 382/U.S. Pat. No. 5 084084/U.S. Pat. No. 5 127 935/U.S. Pat. No. 5,154,755, EP-563 384, DE-4412 079).

The formula (III) provides a general definition of the acyl halidesfurther to be used as starting materials in the process according to theinvention for preparing the compounds of the formula (I). In the formula(III), R⁴ preferably or in particular has that meaning which has alreadybeen indicated above, in connection with the description of thecompounds of the formula (I) to be prepared according to the invention,as being preferred or particularly preferred for R⁴; X preferablyrepresents fluorine, chlorine or bromine, in particular chlorine.

The starting materials of the formula (III) are known chemicals forsynthesis.

The process according to the invention for preparing the compounds ofthe formula (I) ist preferably carried out in the presence of a suitablereaction auxiliary. Suitable reaction auxiliaries are generally thecustomary inorganic or organic bases or acid acceptors. These includepreferably alkali metal or alkaline earth metal acetates, amides,carbonates, bicarbonates, hydrides, hydroxides or alkoxides such as, forexample, sodium acetate, potassium acetate or calcium acetate, lithiumamide, sodium amide, potassium amide or calcium amide, sodium carbonate,potassium carbonate or calcium carbonate, sodium bicarbonate, potassiumbicarbonate or calcium bi-carbonate, lithium hydride, sodium hydride,potassium hydride or calcium hydride, lithium hydroxide, sodiumhydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide orpotassium methoxide, sodium ethoxide or potassium ethoxide, sodium n- ori-propoxide or potassium n- or i-propoxide, sodium n-, i-, s- ort-butoxide or potassium n-, i-, s- or t-butoxide; furthermore also basicorganic nitrogen compounds such as, for example, trimethylamine,triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine,N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine,N,N-dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-,3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl-and3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methyl-piperidine,1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

The process according to the invention for preparing the compounds ofthe formula (I) is preferably carried out in the presence of a diluent.Suitable diluents are generally the customary organic solvents. Thesepreferably include aliphatic, alicyclic and aromatic, optionallyhalogenated hydrocarbons such as, for example, pentane, hexane, heptane,petroleum ether, ligroin, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane,dichloromethane (methylene chloride), trichloromethane (chloroform) ortetrachloromethane, dialkyl ethers such as, for example, diethyl ether,diisopropyl ether, methyl t-butyl ether, ethyl t-butyl ether, methylt-pentyl ether (MTBE), ethyl t-pentyl ether, tetrahydrofuran (THF),1,4-dioxane, ethylene glycol dimethyl ether or ethylene glycol diethylether, diethylene glycol dimethyl ether or diethylene glycol diethylether; dialkyl ketones, such as, for example, acetone, butanone (methylethyl ketone), methyl i-propyl ketone or methyl i-butyl ketone, nitrilessuch as, for example, acetonitrile, propionitrile, butyronitrile orbenzonitrile; amides such as, for example, N,N-dimethyl-formamide (DMF),N,N-dimethyl-acetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethylphosphoric triamide; esters such as, for example, methylacetate, ethyl acetate, n- or i-propyl acetate, n-, i- or s-butylacetate; sulphoxides such as, for example, dimethyl sulphoxide; alkanolssuch as, for example, methanol, ethanol, n- or i-propanol, n-, i-, s- ort-butanol, ethylene glycol monomethyl ether or ethylene glycol monoethylether, diethylene glycol monomethyl ether or diethylene glycol monoethylether; mixtures thereof with water or pure water.

When carrying out the process according to the invention, the reactiontemperatures can be varied over a relatively wide range. In general,temperatures of between −10° C. and +150° C., preferably temperatures ofbetween 0° C. and 100° C., are employed.

The process according to the invention is generally carried out underatmospheric pressure (“normal pressure”). However, it is also possibleto operate under elevated or reduced pressure—in general between 0.1 barand 10 bar.

In the practice of the process according to the invention, the startingmaterials are generally employed in approximately equimolar amounts.However, it is also possible to use one of the components in arelatively large excess. The reaction is generally carried out in asuitable diluent in the presence of a reaction auxiliary, and thereaction mixture is generally stirred for several hours at thetemperature required. Work-up is carried out according to customarymethods (cf. the Preparation Examples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm-killers and, especially, as weed-killers.By weeds, in the broadest sense, are to be understood all plants whichgrow in locations where they are undesired. Whether the substancesaccording to the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera:

Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga,Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium,Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus,Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica,Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,Ranunculus and Taraxacum.

Dicotyledonous crops of the genera:

Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum,Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca,Cucumis and Cucurbita.

Monocotyledonous weeds of the genera:

Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca,Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum,Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis,Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis,Alopecurus and Apera.

Monocotyledonous crops of the genera:

Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum,Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds of the formula (I) are suitable, depending on theconcentration, for the total control of weeds, for example on industrialterrain and rail tracks, and on paths and squares with or without treeplantings. Equally, the compounds can be employed for controlling weedsin perennial cultures, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, onlawns, turf and pasture-land, and for the selective control of weeds inannual crops. The compounds of the formula (I) according to theinvention are particularly suitable for the selective control ofmonocotyledonous and dicotyledonous weeds in mono-cotyledonous cropspre- and post-emergence.

The active compounds are suitable for controlling animal pests,preferably arthropods and nematodes, in particular insects andarachnida, which are encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienefield. They are active against normally sensitive and resistant speciesand against all or some stages of development. The abovementioned pestsinclude:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Pediculus humanus corporis,Haematopinus ssp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Pemphigus spp., Phorodon humuli, Phylloxera vastatrix, Rhopalosiphumpadi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps,Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvatalugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. andPsylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Trotrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoropts spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranuchus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp.,Globodera spp., Meliodogyne spp., Aphelenchoides spp., Longidorus spp.,Xiphinema spp., Trichodorus spp., Tylenchus spp., Helicotylenchus spp.,Rotylenchus spp. and Tylenchulus spp.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activewcompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethyl-formamide anddimethyl sulphoxide, and also water.

As solid carriers there are suitable:

for example ammonium salts and ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly disperse silica,alumina and silicates, as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, as well as syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifying and/or foam-forming agents there are suitable: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates aswell as albumen hydrolysis products; as dispersing agents there aresuitable: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and neutral and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, moybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or,in their formulations, as a mixture with known herbicides for thecontrol of weeds, in which case ready-to-use formulations or tank mixesare possible.

Suitable co-components for the mixture are known herbicides, for exampleanilides such as, for example, diflufenican and propanil; arylcarboxylicacids such as, for example, dichloropicolinic acid, dicamba andpicloram; aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB,2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxyphenoxy-alkanoicesters such as, for example, diclofop-methyl, fenoxaprop-ethyl,fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones suchas, for example, chloridazon and norflurazon; carbamates such as, forexample, chlorpropham, desmedipham, phenmedipham and propham;chloroacetanilides such as, for example, alachlor, acetochlor,butachlor, metazachlor, metolachlor, pretilachlor and propachlor;dinitroanilines such as, for example, oryzalin, pendimethalin andtrifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox,fluoroglycofen, fomesafen, halosafen, lactofen and oxafluorfen; ureassuch as, for example, chlortoluron, diuron, fluometuron, isoproturon,linuron and methabenzthiazuron; hydroxylamines such as, for example,alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim;imidazolinones such as, for example, imazethapyr, mazamethabenz,imazapyr and imazaquin; nitriles such as, for example, bromoxynil,dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet;sulfonylureas such as, for example, amidosulfuron, bensulfuron-methyl,chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl,nicosulfuron, primisulfuron, pyrazosulforon-ethyl,thifensulfuron-methyl, triasulfuron and tribenzuron-methyl;thiocarbamates such as, for example, butylate, cycloate, diallate, EPTC,esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazinessuch as, for example, atrazine, cyanazine, simazine, simetryne,terbutryne and terbutylazine; triazinones such as, for example,hexazinone,metamitron and metribuzin; others such as, for example,aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosphate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use form prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the cutomary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention can be seen from the examples below.

PREPARATION EXAMPLES Example 1

At about 20° C., 0.90 g (5 mmol) of 4-chloro-benzoyl chloride are addedto a mixture of 2.1 g (5 mmol) of1-(4-cyano-5-ethylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluormethyl-1(2H)-pyrimidine,0.60 g (6 mmol) of triethylamine and 50 ml of acetonitrile, and thereaction mixture ist stirred at 20° C. for 2 hours. The mixture is thenconcentrated using waterpump vacuum and the residue is taken up inchloroform, washed with 2N hydrochloric acid, dried with sodium sulphateand filtered. The filtrate is concentrated using waterpump vacuum, theresidue is digested with diethyl ether and the resulting crystallineproduct is isolated by filtration with suction.

1.5 g (54% of theory) of1-[4-cyano-5-(N-ethylsulphonyl-N-(4-chlorobenzoyl)-amino)-2-fluoro-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine of melting point 138° C. areobtained.

Example 2

At about 20° C., 1.8 g (12 mmol) of thiophene-2-carbonyl chloride areadded to a mixture of 2.1 g (5 mmol) ofT-(4-cyano-5-ethylsulphonylamino-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyyrimidine,1.5 ml of pyridine and 50 ml of methylene chloride, and the reactionmixture is stirred at 20° C. for one week. The solution is then washedwith IN hydrochloric acid, dried with sodium sulphate and filtered. Thefiltrate is concentrated using waterpump vacuum, the residue is digestedwith diethyl ether and the resulting crystalline product is isolated byfiltration with suction.

2.1 g (84% of theory) of1-[4-cyano-5-(N-ethylsulphonyl-N-(thien-2-yl-carbonyl)-amino)-2-fluoro-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine of melting point 192° C. areobtained.

By proceeding similarly to Examplex 1 and 2 and according to the generaldescription of the preparative process of the invention, it is alsopossible to prepare, for example, the compounds of the formula (I)listed below in Table 1.

TABLE 1 Examples of compounds of the formula (I) Melting Ex point No. QR¹ R² R³ R⁴ R⁵ R⁶ R⁷ (° C.)  3 O F CN C₂H₅

H CF₃ CH₃  93  4 O F CN C₂H₅

H CF₃ CH₃ 108  5 O F CN C₂H₅

H CF₃ CH₃ 157  6 O F CN C₂H₅

H CF₃ CH₃ 190  7 O F CN C₂H₅

H CF₃ CH₃ 186  8 O F CN C₂H₅

H CF₃ CH₃ 206  9 O F CN C₂H₅

H CF₃ CH₃ 123 10 O F CN C₂H₅

H CF₃ CH₃ 191 11 O F CN CH₃

H CF₃ CH₃ 215 12 O F CN CH₃

H CF₃ CH₃ 189 13 O F CN CH₃

H CF₃ CH₃ 189 14 O F CN CH₃

H CF₃ CH₃ 201 15 O F CN CH₃

H CF₃ CH₃ 175 16 O F CN CH₃

H CF₃ CH₃ 184 17 O F CN CH₃

H CF₃ CH₃ 193 18 O F CN CH₃

H CF₃ CH₃ 203 19 O F CN CH₃

H CF₃ CH₃ 202 20 O H CN CH₃

H CF₃ CH₃ 21 O Cl Cl CH₃

H CF₃ CH₃ 22 O H CN C₂H₅

H CF₃ CH₃ 23 O F CN n-C₃H₇

H CF₃ CH₃ 24 O F CN n-C₄H₉

H CF₃ CH₃ 25 O F CN CH₃

H CF₃ C₂H₅ 26 O Cl CN CH₃

H CF₃ CH₃ 27 O Cl CN CH₃

H CF₃ CH₃ 28 O Cl CN n-C₃H₇

H CF₃ CH₃ 29 O F CN i-C₃H₇

CH₃ CF₃ C₂H₅ 30 O F CN

H CF₃ CH₃ 31 O F CN n-C₄H₉

H CF₃ NH₂ 32 O F CN i-C₄H₉

H CF₂Cl CH₃ 33 O Cl

CH₃

H CF₃ CH₃ 34 O F

CH₃

H C₂F₅ CH₃ 35 O F CN CH₃

H CF₃ CH₃ 36 O F CN CH₃

H CHF₂ CH₃ 37 O F CN C₂H₅

H CF₃ CH₃ 38 O F CN CH₃

H CF₃ CH₃ 39 O F CN CH₃

H CF₃ CH₃ 40 O F CN CH₃

H CF₃ CH₃ 41 O F CN C₂H₅

H CHF₂ CH₃ 42 O F CN C₂H₅

H CF₃ CH₃ 43 O F CN CH₃

H CF₃ CH₃ 44 O F CN CH₃

H CF₃ CH₃ 45 O F CN CH₃

H CF₃ CH₃ 46 O F CN CH₃

H CF₃ NH₂ 268 47 S F CN C₂H₅

CH₃ CF₃ CH₃ 48 O F CN n-C₃H₇

H CF₃ CH₃ 49 O F CN CH₃

H CF₃ CH₃ 50 O F CN CH₃

H CF₃ CH₃ 51 S F CN CH₃

H CF₃ CH₃ 52 S F CN CH₃

H CF₃ CH₃ 53 S F CN CH₃

H CF₃ CH₃ 54 S F CN CH₃

H CF₃ CH₃ 55 S F CN CH₃

H CF₃ CH₃ 56 O F CN CH₃

H CF₃ CH₃ 57 O F CN CH₃

H CF₃ CH₃ 58 O F CN CH₃

H CF₃ CH₃ 59 O F CN C₂H₅

H CF₃ CH₃ 173 60 O F CN C₂H₅

H CF₃ CH₃ 192 61 O F CN C₂H₅

H CF₃ CH₃ 188 62 O F CN C₂H₅

H CF₃ CH₃ 188 63 O F CN C₂H₅

H CF₃ CH₃ 122 64 O F CN C₂H₅

H CF₃ CH₃ 164 65 O F CN C₂H₅

H CF₃ CH₃ 159 66 O F CN C₂H₅

H CF₃ CH₃ 107 67 O F CN C₂H₅

H CF₃ CH₃ 198 68 O F CN C₂H₅

H CF₃ H 187 69 O F CN C₂H₅

H CF₃ NH₂ 120 70 O F CN CH₃

H CF₃ CH₃ 227 71 O F CN CH₃

H CF₃ CH₃ 241 72 O F CN CH₃

H CF₃ CH₃ 219 73 O F CN CH₃

H CF₃ CH₃ 199 74 O F CN CH₃

H CF₃ CH₃ 178 75 O F CN CH₃

H CF₃ CH₃ 222 76 O F CN CH₃

H CF₃ CH₃ 225 77 O F CN CH₃

H CF₃ CH₃ 195 78 O F CN CH₃

H CF₃ CH₃ 216 79 O F CN C₂H₅

H CF₃ NH₂  89 80 O F CN C₂H₅

H CF₃ NH₂ 105 81 O F CN C₂H₅

H CF₃ NH₂ >200   82 O F CN C₂H₅

H CF₃ CH₃ 127 83 O F CN C₂H₅

H CF₃ H 170 84 O F CN C₂H₅

H CF₃ H 197 85 O F CN C₂H₅

H CF₃ NH₂ 177 86 O F CN C₂H₅

H CF₃ NH₂ 210 87 O F CN C₂H₅

H CF₃ CH₃ 156 88 O F CN C₂H₅

H CF₃ CH₃ 179 89 O F CN C₂H₅

H CF₃ H 108 90 O F CN C₂H₅

H CF₃ H 217 91 O F CN C₂H₅

H CF₃ H 227 92 O F CN C₂H₅

H CF₃ CH₃ (amorph) 93 O F CN C₂H₅

H CF₃ CH₃ 188 94 O F CN C₂H₅

H CF₃ CH₃ (amorph) 95 O F CN C₂H₅

H CF₃ H 237 96 O F CN C₂H₅

H CF₃ NH₂ 149 97 O F CN C₂H₅

H CF₃ H 213 98 O F CN C₂H₅

H CF₃ H 227 99 O F CN C₂H₅

H CF₃ H 237 100  O F CN C₂H₅

H CF₃ NH₂ 237 101  O F CN C₂H₅

H CF₃ NH₂ 205 102  O F CN C₂H₅

H CF₃ NH₂ 185 103  O F CN C₂H₅

H CF₃ NH₂ 240 104  O F CN C₂H₅

H CF₃ NH₂ (amorph) 105  O F CF₃ C₂H₅

H CF₃ CH₃ (amorph) 106  O F CF₃ C₂H₅

H CF₃ CH₃ (amorph) 107  O F CF₃ C₂H₅

H CF₃ NH₂ 226 108  O F CF₃ C₂H₅

H CF₃ NH₂ 193 109  O F CN C₂H₅

H CF₃ CH₃ 148 110  O F CN CH₃

H CF₃ NH₂ 216 111  O F CN CH₃

H CF₃ NH₂ 160 112  O F CN CH₃

H CF₃ NH₂ 152 113  O F CN CH₃

H CF₃ NH₂ 208 114  O F CF₃ CH₃

H CF₃ CH₃ 180 115  O F CF₃ CH₃

H CF₃ CH₃ 196 116  O F CF₃ CH₃

H CF₃ CH₃ 209 Ex. No. Q R¹ R² R³ R⁴ R⁵ R⁶ R⁷ log-P 117  O F CN C₂H₅

H CF₃ CH₃ 3,59 118  O F CN C₂H₅

H CF₃ CH₃ 3,54 119  O F CN C₂H₅

H CF₃ CH₃ 3,17 120  O F CN C₂H₅

H CF₃ CH₃ 3,72 121  O F CN C₂H₅

H CF₃ CH₃ 3,19 122  O F CN C₂H₅

H CF₃ CH₃ 3,77 123  O F CN C₂H₅

H CF₃ CH₃ 3,55 124  O F CN C₂H₅

H CF₃ CH₃ 3,86 125  O F CN C₂H₅

H CF₃ CH₃ 3,47 126  O F CN C₂H₅

H CF₃ CH₃ 3,92 127  O F CN C₂H₅

H CF₃ CH₃ 3,50 128  O F CN C₂H₅

H CF₃ CH₃ 2,38 129  O F CN C₂H₅

H CF₃ CH₃ 2,90 130  O F CN C₂H₅

H CF₃ CH₃ 3,86 131  O F CN C₂H₅

H CF₃ CH₃ 3,35 132  O F CN C₂H₅

H CF₃ CH₃ 3,74 133  O F CN C₂H₅

H CF₃ CH₃ 3,59 134  O F CN C₂H₅

H CF₃ CH₃ 3,32 135  O F CN C₂H₅

H CF₃ CH₃ 3,15 136  O F CN C₂H₅

H CF₃ CH₃ 5,42 137  O F CN C₂H₅

H CF₃ CH₃ 3,66 138  O F CN C₂H₅

H CF₃ CH₃ 3,46 139  O F CN C₂H₅

H CF₃ CH₃ 3,38 140  O F CN C₂H₅

H CF₃ CH₃ 3,37 141  O F CN C₂H₅

H CF₃ CH₃ 3,57 142  O F CN C₂H₅

H CF₃ CH₃ 3,75 143  O F CN C₂H₅

H CF₃ CH₃ 3,24 144  O F CN C₂H₅

H CF₃ CH₃ 3,41 145  O F CN C₂H₅

H CF₃ CH₃ 3,58 146  O F CN C₂H₅

H CF₃ CH₃ 3,33 147  O F CN C₂H₅

H CF₃ CH₃ 5,29 148  O F CN C₂H₅

H CF₃ CH₃ 3,73 149  O F CN C₂H₅

H CF₃ CH₃ 2,95 150  O F CN C₂H₅

H CF₃ CH₃ 3,74 151  O F CN C₂H₅

H CF₃ CH₃ 4,15 152  O F CN C₂H₅

H CF₃ CH₃ 3,30 153  O F CN C₂H₅

H CF₃ CH₃ 3,62 154  O F CN C₂H₅

H CF₃ CH₃ 3,39 155  O F CN C₂H₅

H CF₃ CH₃ 3,10 156  O F CN C₂H₅

H CF₃ CH₃ 3,04 157  O F CN C₂H₅

H CF₃ CH₃ 3,37 158  O F CN C₂H₅

H CF₃ CH₃ 3,70 159  O F CN C₂H₅

H CF₃ CH₃ 3,62 160  O F CN C₂H₅

H CF₃ CH₃ 161  O F CN C₂H₅

H CF₃ CH₃ 162  O F CN C₂H₅

H CF₃ CH₃ 163  O F CN C₂H₅

H CF₃ CH₃ 164  O F CN C₂H₅

H CF₃ CH₃ 165  O F CN C₂H₅

H CF₃ CH₃ 166  O F CN C₂H₅

H CF₃ CH₃ 167  O F CN C₂H₅

H CF₃ CH₃ 168  O F CN C₂H₅

H CF₃ CH₃ 169  O F CN C₂H₅

H CF₃ CH₃

The determination of the log-P values was carried out according to theEEC-Directive 79/831 Annex V. A8 using HPLC (gradient method,acetonitrile/0,1% aqueous phosphoric acid).

USE EXAMPLES Example A

Pre-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered or sprayed with the preparation of the active compound. It isadvantageous to keep the amount of water per unit area constant. Theconcentration of the active compound in the preparation is immaterial,only the amount of active compound applied per unit area matters. Afterthree weeks, the degree of damage to the plants is rated in % damage bycomparison with the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, very strong activity against weeds such as cyperus(60-100%), lolium (70-90%), panicum (70-95%), abutilon (100%),chenopodium (100%) and datura (100%) is shown, for example, by thecompounds of Preparation Examples 1 and 2 at an application rate of 60g/ha, combined with very good tolerance by crops such as, for example,maize (0%).

Example B

Post-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the particular mixedamounts of active compound are applied in 1000 1/ha. After three weeks,the degree of damage to the plants is rated in % damage by comparisonwith the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

In this test, very strong activity against weeds such as echinochloa(95%), sorghum (70-80%), abutilon (100%), chenopodium (100%), datura(100%) and solanum (100%) is shown, for example, by the compounds ofPreparation Examples 1 and 2 at an application rate of 30 g/ha, combinedwith good tolerance by crops such as, for example, barley (0-10%).

Example C

Phaedon Larvae Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with mustard beetle larvae (Phaedon cochleariae) while theleaves are still moist.

After the desired period of time, the destruction in % is determined.100% means that all the beetle larvae have been killed; 0% means thatnone of the beetle larvae have been killed.

In this test, a destruction of 80 to 100% was caused, after 7 days, forexample by the compounds of Preparation Examples 1 and 2 at an activecompound concentration of 0,1%.

Example D

Nephotettix Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of the active compound of the desired concentration and areinfested with larvae of the green rice leafhopper (Nephotettixcincticeps) while the seedlings are still moist.

After the desired period of time, the destruction in % is determined.100% means that all the leafhoppers have been killed; 0% means that noneof the leafhoppers have been killed.

In this test, a destruction of 100% was caused, after 6 days, forexample by the compounds of Preparation Examples 1 and 2 at an activecompound concentration of 0,1%.

What is claimed is:
 1. A compound of formula (I)

wherein Q is oxygen or sulphur; R¹ is hydrogen, cyano, fluorine orchlorine; R² is cyano; R³ is an optionally substituted alkyl having 1 to6 carbons, wherein the substituents are cyano-, fluorine-, chlorine-,bromine-, C₁-C₄-alkoxy- or C₁-C₄-alkylthio; or R³ is an optionallysubstituted cycloalkyl having 3 to 8 carbon atoms cyano-, fluorine-,chlorine-, bromine- or C₁-C₄-alkyl-; R³ is optionally substitutedphenyl, naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl, pyridinyl orquinolinyl, wherein substituents are: fluorine, chlorine, bromine,cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-alkylthio, dimethylaminosulphonyl,diethylaminosulphonyl, optionally C₁-C₄-alkylsulphinyl orC₁-C₄-alkylsulphonyl, wherein the substituents are fluorine- orchlorine-, optionally substituted C₁-C₄-alkoxycarbonyl, wherein thesubstituents are fluorine-, chlorine-, bromine-, cyano-, methoxy- orethoxy-, optionally substituted phenyl, phenyloxy or phenylthio whereinthe substituents are fluorine-, chlorine-, bromine-, cyano-, methyl-,methoxy-, trifluoromethyl- or trifluoromethoxy-; R⁴ is a substitutedphenyl wherein the substituents are: fluorine, chlorine, bromine, cyano,nitro, carboxy, carbamoyl, thiocarbamoyl, dimethylamino,dimethylaminosulphonyl, diethylaminosulphonyl, optionally substitutedC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl orC₁-C₄-alkylsulphonyl, wherein the substituents are fluorine- orchlorine-, optionally substituted C₁-C₄-alkoxycarbonyl, wherein thesubstituents are fluorine-, chlorine-, bromine-, cyano-, methoxy- orethoxy-; R⁵ is hydrogen, fluorine, chlorine, bromine or is an optionallysubstituted alkyl or alkoxy having in each case 1 to 4 carbon atoms,wherein the substituents are fluorine- or chlorine-; R⁶ is an optionallysubstituted alkyl having 1 to 4 carbon atoms, wherein he substituentsare fluorine- or chlorine-; and R⁷ represents hydrogen, hydroxyl, aminoor optionally substituted alkyl, alkoxy, alkenyl or alkinyl having ineach case up to 6 carbon atoms wherein the substituents are fluorine-,chlorine- or C₁-C₄-alkoxy-.
 2. The compound according to claim 1 whereinQ is oxygen or sulphur; R¹ is hydrogen, cyano, fluorine or chlorine; R²is cyano; R³ is an optionally substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, wherein the substiuents are cyano-, fluorine-,chlorine-, methoxy-or ethoxy-, R³ is an optionally substitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, wherein thesubstituents are cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, R³ is an optionally substituted phenyl,naphthyl, benzyl, phenylethyl, thienyl, pyrazolyl, pyridinyl, orquinolyl, wherein the substituents are: fluorine, chlorine, bromine,cyano, nitro, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- ori-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl,dimethylaminosulphonyl, diethylaminosulphonyl, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl; R⁴ is a substituted phenylwherein the substituents are: fluorine, chlorine, bromine, cyano, nitro,carboxy, carbamoyl, thiocarbamoyl, dimethylamino, dimethylaminosulphonylor diethylaminosulphonyl, optionally substituted methyl, ethyl, n- ori-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, wherein thesubstituents are fluorine-, chlorine-, optionally substitutedmethoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, wherein thesubstituents are fluorine-, chlorine-, bromine-, cyano-, methyl-,methoxy-, ethoxy, optionally substituted phenyl, phenyloxy orphenylthio, wherein the substituents are fluorine-, chlorine-, bromine-,cyano-, methyl-, methoxy-, trifluoromethyl- and/or trifluoromethoxy-; R⁵is hydrogen, fluorine, chlorine, bromine or an optionally substitutedmethyl, ethyl, n- or i-propyl, wherein the substituents are fluorine- orchlorine-; R⁶ is optionally substituted methyl, ethyl, n- or i-propyl,wherein the substituents are fluorine- or chlorine-; and R⁷ is hydrogen,amino or an optionally substituted methyl, ethyl, n- or i-propyl, n-, i-or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy,propenyl, butenyl, propinyl or butinyl, wherein the substituents arefluorine or chlorine.
 3. A method for controlling unwanted vegetationwhich comprises applying to such vegetation or to a locus from which itis desired to exclude such vegetation an herbicidally effective amountof the compound according to claim
 1. 4. An herbidical composition whichcomprises the compound according to claim 1 and an extender orsurfactant.